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In their first move of the offseason, the Boston Celtics traded veteran guard Jrue Holiday back to the Portland Trail Blazers in exchange for guard Anfernee Simons and a pair of second-round picks. Two weeks later, the deal is official, but the terms aren't the same.
The Blazers didn't love Holiday's medical records, per Aaron J. Fentress of The Oregonian, and sought to diminish their initial trade package. The Celtics will still receive Simons for Holiday, yet there will be no draft picks involved.
Holiday, who turned 35 in June, missed just 20 games last regular season. However, he played through a mallet finger injury for a fair chunk of the 2024-25 campaign and was sidelined for three games in the first round of the playoffs due to a hamstring issue.
It's not clear what exact health problem the Blazers were troubled by. Either way, they still wanted Holiday, a two-time NBA champion who spent four days with them in 2023 before shipping off to Boston and immediately making his winning presence felt.
“A recent review of Holiday’s medicals revealed nothing substantial enough to warrant the trade being negated,” Fentress reported. “However, there was enough there to lead the Blazers to slightly alter the terms of the deal.”
While the Celtics are left without a pair of picks, they currently have a sizable stash of second-round selections that they can use as trade bait down the line. Since the C's are without star Jayson Tatum for the foreseeable future because of a devastating Achilles injury, they look like a work in progress, and the front office will likely make another move in the coming weeks to address that feeling of incompletion.
Whether or not Simons is a part of Boston's long-term plan remains to be seen, yet there's no denying his scoring ability. That could prove particularly useful for the 2025-26 season when the Celtics are down their leading scorer and no longer roster two other starters — Holiday and center Kristaps Porzingis — from their 2024 championship core.
Although Simons' defense is lackluster, especially in comparison to Holiday, he's shot over 35% from deep in five straight seasons and has averaged 15 points per game over the course of his seven-year career.
The 6-foot-3 guard is also nine years younger than Holiday and on an expiring deal, which works well given the Celtics' current money situation. That doesn't mean Boston won't miss Holiday, though, as its entire roster was ringless before he arrived in 2023 and helped them win that elusive title.
